3-(phenylthio)propanal dimethyl acetal | 52072-17-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)propanal dimethyl acetal
• 英文别名: 1,1-dimethoxy-3-(phenylthio)propane；[(3,3-dimethoxypropyl)thio]-benzene；1,1-Dimethoxy-3-(phenylthio)-propan；[(3,3-Dimethoxypropyl)sulfanyl]benzene；3,3-dimethoxypropylsulfanylbenzene
• CAS: 52072-17-0
• 化学式: C₁₁H₁₆O₂S
• 分子量: 212.313
• InChiKey: MFWBNWMSEJYYBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(phenylthio)propanal dimethyl acetal 在 盐酸 、 六甲基磷酰三胺 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.33h， 生成 1-[3-(phenylthio)cyclopent-1-enyl]propan-1-one
  参考文献：
  名称：

  Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function

  摘要：

  1,1-Dimethyl-3-(phenyldio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCl was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01248-0
• 作为产物：
  描述：

  3-(phenylthio)-3-methoxypropene 在 甲烷磺酸 、 三氟甲磺酸 作用下， 以 乙醚 为溶剂， 反应 23.0h， 生成 3-(phenylthio)propanal dimethyl acetal
  参考文献：
  名称：

  Heteroatom-directed allylic substitution and rearrangement reactions

  摘要：

  DOI：

  10.1021/jo00381a014

文献信息

• The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
  作者：J.V. Comasseto、E.S. Lang、J. Tercio、B. Ferreira、F. Simonelli、V.R. Correia

  DOI：10.1016/0022-328x(87)80095-5

  日期：1987.11

  quenched by alkyl and activated aryl halides to give the corresponding sulfides and selenides in high yield (77–97%). The aryltellurolates react with alkyl halides giving the aryl alkyl tellurides in 81–96% yield. The procedure could not be successfully used for the synthesis of dialkylselenides and dialkyl tellurides; low yields and mixture of products were formed.

  描述了一种方法，该方法允许在相转移条件下从相应的二有机二硫代碳酸酯开始原位合成芳基烷基，二芳基和二烷基硫属化物。在碱性介质中，氨基亚氨基甲烷亚磺酸（二氧化硫脲）可还原二氰化物，并由季铵盐催化。对于二芳基二硫化物和二芳基二硒化物，在氢氧化钠浓度为13％时，还原很容易进行；二芳基二碲化物需要50％的氢氧化钠溶液以生成芳基碲酸根阴离子。二烷基二硒化物和二烷基二碲化物更难以还原。用烷基和活化的芳基卤化物淬灭中间体芳基硫醇盐和芳基硒酸酯，可以高产率（77-97％）得到相应的硫化物和硒化物。芳碲酸铝盐与烷基卤化物反应，得到芳基烷基碲化物，收率为81–96％。该方法不能成功地用于合成二烷基硒化物和二烷基碲化物。收率低并且形成了产物的混合物。
• Synthesis of 3-Acylfurans Using 3-(Phenylthio)propanal Dimethyl Acetal as a New Synthon. Syntheses of Ipomeanine and Isoegomaketone
  作者：Eiji Watanabe、Naohiro Imai、Katsuhiko Inomata、Hideki Kinoshita、Hiroshi Kotake

  DOI：10.1246/bcsj.55.3225

  日期：1982.10

  It was found that 3-(phenylthio)propanal dimethyl acetal is a very useful starting material for the preparation of 3-acylfuranoterpenes. Syntheses of two naturally-occurring furans, isoegomaketone and ipomeanine were described.

  发现3-(苯硫基)丙醛二甲基缩醛是用于制备3-酰基呋喃萜的非常有用的起始原料。描述了两种天然呋喃、异己酮和伊波米宁的合成。
• Directed addition of sulfur-stabilised carbanions to 1,2,3-trisubstituted aziridines
  作者：Donald Craig、Pengfei Lu、Tanya Mathie、Niels T.H. Tholen

  DOI：10.1016/j.tet.2010.04.096

  日期：2010.8

  Thioether and sulfone-stabilised carbanions possessing varying functional groups enter into highly regioselective, stereospecific ring-opening reactions with vinyl- and hydroxymethyl-substituted aziridines. Some derivatisation reactions of the adducts are reported. (C) 2010 Elsevier Ltd. All rights reserved.
• Template-directed intramolecular C-glycosidation. Total synthesis of acid
  作者：Donald Craig、Mark W. Pennington、Peter Warner

  DOI：10.1016/0040-4039(95)01104-p

  日期：1995.8
• Behzadi,A.; Owen,L.N., Journal of the Chemical Society. Perkin transactions I, 1974, p. 25 - 29
  作者：Behzadi,A.、Owen,L.N.

  DOI：——

  日期：——